4,8-dihydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one

• ChemBase ID: 154340
• Molecular Formular: C19H16O5
• Molecular Mass: 324.32734
• Monoisotopic Mass: 324.09977361
• SMILES: CC(=O)CC(c1ccccc1)c1c(c2cccc(c2oc1=O)O)O
• Canonical SMILES: CC(=O)CC(c1c(=O)oc2c(c1O)cccc2O)c1ccccc1
• InChI: InChI=1S/C19H16O5/c1-11(20)10-14(12-6-3-2-4-7-12)16-17(22)13-8-5-9-15(21)18(13)24-19(16)23/h2-9,14,21-22H,10H2,1H3
• InChIKey: BHBOXPNWDGYJNB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,8-dihydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one
• IUPAC Traditional name: 4,8-dihydroxy-3-(3-oxo-1-phenylbutyl)chromen-2-one
• Synonyms: 4,8-Dihydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one; 3-(α-Αcetonylbenzyl)-4,8-dihydroxycoumarin; 8-Hydroxy Warfarin; 3-(α-Acetonylbenzyl)-4,8-dihydrocoumarin; 4-8-Dihydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one; 8-Hydroxywarfarin

Database IDs

• CAS Number: 17834-04-7
• MDL Number: MFCD00272667
• PubChem SID: 162248479
• PubChem CID: 54697550

CALCULATED PROPERTIES

• Acid pKa: 6.014071
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.9753466
• LogD (pH = 7.4): 1.7029098
• Log P: 3.091142
• Molar Refractivity: 88.841 cm^3
• Polarizability: 33.955616 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: white; White Solid
• Melting Point: 185-187 °C; 190-192°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Empirical Formula (Hill Notation): C19H16O5

DETAILS

Sigma Aldrich - UC210

Biochem/physiol Actions
Minor CYP1A2 metabolite of (R)-warfarin

Toronto Research Chemicals - H996140

A metabolite of Warfarin (W498500) in humans.

REFERENCES

• Nelsestuen, G., et al.: J. Biol. Chem., 249, 6347 (1974)
• Zhang, Z., et al.: Drug Metab. Dispos., 23, 1339 (1974)
• Evans, W., et al.: Science, 286, 487 (1974)